Inside R. Kelly's Most Shocking Sex Scandals Over the Years, None of Which Derailed His Success in Any Perceivable Way

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On Aug. 31, 1994, R. Kelly married Aaliyah at a hotel in Rosemont, Ill. He was 27. She was 15, but the marriage certificate falsely listed her age as 18. The union was annulled months later. At the 1994 Billboard Music Awards that December, R. Kelly called Aaliyah, whom he had first met when she was 12, his “best friend in the whole, wide world.”

In 1998, R. Kelly won three Grammys for “I Believe I Can Fly,” to date his most successful single. His questionable relationship with Aaliyah relegated to an asterisk at the time and not altogether widely known outside of the industry and hardcore R&B enthusiasts, the Recording Academy heartily rewarded the “Bump N Grind” singer for his Space Jam anthem—and continued to recognize him with 19 more nominations between then and 2015. Devoted fans continued to buy albums and go to concerts, while casual listeners popped in whenever a hit such as the infectious “Ignition (Remix)” or the much hyped “Trapped in the Closet” went mainstream. Fellow artists continued to sign up to collaborate, including Jay-Z, Jennifer Hudson, Justin Bieber and Lady Gaga.

If only that weird blip of a marriage, born of a premature connection they had in the studio while working on Aaliyah’s 1994 debut album, Age Ain’t Nothing But a Number, had been it.

But though the legal quagmires he’s found himself in have largely panned out in his favor, R. Kelly has an increasingly disturbing history when it comes to allegations of misconduct with underage girls and women who claim he’s more Svengali than smooth operator. In August a new round of allegations, including that he paid a woman not to talk about having a relationship with him when she was underage (through his attorney he firmly denied the claim as reported by Buzzfeed News), re-shined the spotlight on a sordid timeline that goes back more than 20 years.

Now Kelly (who was born Robert Sylvester Kelly) is denying claims made by KittiJones to Rolling Stone that she was in an abusive relationship with the singer for two years, during which, Jones said, she quit her job and moved to Chicago to be with him and he attempted to control nearly every move she made.

“Mr. Kelly is aware of the repeated and now evolving claims of Ms. Kanika “Kitti” Jones,” a rep for Kelly said in a statement sent to E! News. “It is unfortunate that Ms. Jones, after public statements to the contrary, is no attempting to portray a relationship history with Mr. Kelly as anything other than consensual involvement between two adults. As stated previously, Mr. Kelly does not control the decision-making or force the actions of any other human being, including Ms. Jones, by her own admission. Any claim of wrongdoing of any kind or of mistreatment of any woman by him is false, ill-motived and defamatory.”

Jones was previously one of three women who told Buzzfeed that he controlled their phone and social media use while they were dating, and that the Grammy winner had multiple young women, ranging in age from 18 to 25, living in his Georgia “guest house” or Chicago recording studio a year ago, and that those women had to ask Kelly’s permission to come and go.

Perhaps the Aaliyah marriage only fazed so many because celebrity history is creepily full of earlier-than-May-to-December romance. Elvis Presley met Priscilla Presley when she was 14 (but courted her for eight years before they married), and Jerry Lee Lewis married his cousin when she was 13 and he was 22 (and his career never fully recovered, though he’s still considered a rock ‘n’ roll legend to this day).

And there’s an even longer history of the industry (and audiences) forgiving artists their scandals.

“When people ask me, I tell them, ‘Hey, don’t believe all that mess. We’re close and people took it the wrong way,” Aaliyah told journalist Jim DeRogatis in December 1994. DeRogatis, the reporter who seven years later was sent a copy of the tape that would lead to child porn charges being filed against Kelly in 2002, has been following and reporting on the invariably stomach-churning allegations against Kelly ever since.

“I would say I loved ‘liyah,” R. Kelly told GQ last year. Asked if he would say “in love,” he replied, “Well, there’s a lot of ways to be in love with a person. I was in love with my grandfather, you know. But yeah, I would say I was in love with Aaliyah just like I was in love with anybody else. But in a different, friend type of way.”

Aaliyah, who was killed in a plane crash in 2001, when she was only 22, sued in 1997 to have the fake marriage certificate expunged and it was promptly sealed. Vibe magazine had published it in 1995.

Kelly told GQ that, “out of respect for her mother who’s sick and her father who’s passed,” he wouldn’t comment further on their relationship. “Out of respect for Aaliyah, and her mother and father who has asked me not to personally,” he said. “But I can tell you I loved her, I can tell you she loved me, we was very close. We were, you know, best best best best friends.”

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A young woman named Tiffany Hawkins sued Kelly in 1996 for allegedly “engaging in inappropriate sexual contact,” including “group sexual sexual intercourse with [her] and other minors” several years prior, when she was 15 and he was 24.

Hawkins was asking for at least $10 million in damages. Kelly immediately counter-sued for defamation; the Chicago Sun-Times reported that Kelly settled for $250,000 in 1998, though his attorney would only confirm that the two sides reached a confidential settlement. “I’m not trying to down him, because I honestly think it has to be a sickness,” a friend of Hawkins, who had planned to testified on her behalf at trial, told the paper. “Looking at pictures of me and Tiffany when we were freshmen—boy, we were ugly little girls compared to what he could have had, so I didn’t understand why he did what he did.”

Also in 1996, Kelly married Andrea Lee, whom he’d first met in 1994—she was 20—when she auditioned to be a dancer on his 12 Play Tour. He and Lee would go on to have three children together, Joann, Jay and Robert Jr., before separating in 2005 and divorcing in 2009.

It was a December 2000 report in the Chicago Sun-Times that first detailed Hawkins’ lawsuit and the full legal story of what happened with Aaliyah, as well as revealed that Kelly had twice been under criminal investigation for allegedly having sex with an underage girl. Both investigations ended when the girl wouldn’t cooperate with authorities. As far as Aaliyah stood, “When R. Kelly comes up, she doesn’t even speak his name, and nobody’s allowed to ask about it at all,” a rep for Virgin Records told the paper.

Tracey Sampson, who claimed she had a 10-month relationship with Kelly that started in May 2000 when she was 17 and working as an intern at Epic Records, sued the singer in 2001 for $50,000.

In February 2002, an anonymous tipster sent an almost 27-minute tape to Jim DeRogatis at the Sun-Times which appeared to show Kelly having sex with a very young woman.

Days later, Kelly performed at the 2002 Winter Olympics Opening Ceremony in Salt Lake City while Chicago police investigated.

“It’s very difficult for me, but you know, I’m innocent,” he told Chicago’s WMAQ-TV before he performed, insisting the tape was a fake and floating a theory about disgruntled former employees or acquaintances being out to get him. “So it’s not that difficult. It’s crap, and that’s how we’re going to treat it.”

Kelly continued, “The reason these things are happening, I really do believe, is because of the fact that I didn’t fall back as far as blackmail was concerned. I didn’t give them any money… All I know is this—I have a few people in the past that I’ve fired… people that I’ve thought were my friends that’s not my friends. Ever since then, it’s been threats on what they’re gonna do to me, and…if I don’t pay them this, they’ll put a story out…and when I refuse to pay them, and now here come this story…The world is getting ready to watch me sing a song called ‘The World’s Greatest,’ and you’ve got a tape out there trying to ruin my career.”

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He settled Sampson’s lawsuit soon after and, after protesters smashed R. Kelly CDs outside the studio of WGCI-FM radio, he called in to offer no excuse for the tape, but to encourage his fans to stand by him. “When you’re famous, they expect you to work miracles, and I’m not God,” he told the station, per MTV News. Sampson’s lawyer said that she had two other female clients who planned to file similar suits against him.

Meanwhile, he and Jay-Z had just released their collaborative album The Best of Both Worlds (which went platinum) that March.

In April 2002, a 20-year-old woman sued Kelly for alleged sexual assault, claiming he had impregnated her when she was a teenager and then forced her to have an abortion. They had sex between 20 and 30 times before she turned 17 (the age of consent in Illinois), resulting in her pregnancy in 1999, plaintiff Patrice Jones claimed in the suit.

“Enough is enough,” Kelly’s attorney Gerald Margolis said told reporters at a press conference in response to Jones’ complaint. “Perhaps…people have gotten the idea that R. Kelly is some sort of walking ATM machine they can hit up for cash simply by threatening to sue him. The cash machine is closed…In the past, we’ve taken the high road with regard to a series of terrible allegations made against Robert. Rather than going to court to defend him against these charges, a process that would have degraded everyone concerned, we decided to settle the cases quietly. This latest suit is a collection of half-truths, distortions and outright lies that we intend to fight and beat.” (The suit was later settled out of court.)

Also in April 2002, the girl in the tape, which had still not been fully authenticated by authorities, was purportedly identified by her aunt, a rapper who had worked with Kelly. She said her niece looked to be about 14 in the video. He in turn insisted that the aunt, Stephanie Edwards (who went by the stage name Sparkle), had a beef with him. “I’m no angel, but I’m no monster, either,” he told MTV News that May, further insisting he was innocent.

Asked if he had ever taped himself having sex, Kelly said, “I’ve done a lot of things that I regret. I’ve done a lot of things that are wrong, but unfortunately we don’t have a lot of time to lay out all of my sins. I wish that I could, but I’m dealing with it. I got a lot that’s in me that I’m dealing with personally.” He hadn’t watched the tape in question, he said, because “why would I want to see something that disgusting and crazy?” He added, “Maybe when all of this is over I’ll say, ‘Let me see that thing.’ But right now it doesn’t make sense for me to want to see something that is not me…I have no interest in seeing some man with a woman whether she’s underage or not underage. I have no interest in that.”

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Kelly was sued again in May 2002, this time for invasion of privacy for allegedly secretly taping a sexual encounter with the plaintiff, Montina Wood. (Wood reportedly accepted money in exchange for signing an NDA.)

As the civil suits piled up, the criminal investigation also continued, and in June 2002 Kelly was arrested and charged in Chicago with 21 counts of child pornography. He maintained his innocence and remained free on a $750,000 bond.

In July 2002, Editor & Publisher scolded the Sun-Times in an article stating that the newspaper was beholden to the public, not the police, and erred in having DeRogatis turn the tape over to police, after which they reported on the investigation without revealing police had gotten the tape in the first place from the paper. Once the investigation was underway, the journalism watchdog continued, the Sun-Times also should have duly reported that the girl and her parents had testified before a grand jury that it was not her in the tape.

The following January, 2003, Kelly was charged in Florida with 16 counts of child porn after authorities allegedly found nude photos of underage girls on a camera at his house. He pleaded not guilty. Also that month, his new album, Chocolate Factory, debuted at No. 1 on the Billboard 200. The biggest change in his day-to-day life was having to ask permission from Illinois and Florida authorities to travel, permission that was usually granted.

In February 2004, seven of the 21 charges in Chicago were dropped. Weeks later all of the Florida charges were dismissed due to a technicality having to do with the search warrant.

His double album Happy People/U Saved Me dropped in August and debuted at No. 2.

Meanwhile, he and Jay-Z had teamed up again for the album Unfinished Business and, in a tacit show of support from the rapper, they headed out as co-headliners on the Best of Both Worlds Tour that summer. After several displays of erratic behavior on Kelly’s part, Jay-Z pulled the plug on the final 15 dates of the tour. The final straw came when Kelly made a spectacle onstage at Madison Square Garden, accusing audience members of waving guns and stopping the show despite, as he later admitted, not actually seeing any guns with his own eyes.

Unfinished Business dropped that October and reached No. 1.

Later in November 2004, Kelly was linked to another sex tape, this one reportedly showing him having sex with baseball player Gary Sheffield‘s wife 10 years prior, when she was a teenager. A man was later convicted of extortion for trying to collect money from Sheffield in exchange for not releasing the tape.

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Kelly’s wife, Andrea, filed for a restraining order against him in September 2005, alleging he got violent when she asked for a divorce. She later dropped the claim but reportedly moved out of the house they shared.

Also that year, Kelly’s TP.3 Reloaded, featuring portions of the conversation starter “Trapped in the Closet,” debuted at No. 1.

A trial date of Sept. 17, 2007, was finally set in Kelly’s child porn case. Despite being estranged, Lee spoke out in May 2007, insisting that wasn’t her husband in the sex tape (though she admitted she hadn’t seen it). The trial start date was subsequently delayed to May 8, 2008, to allow for the lead prosecutor’s maternity leave.

Before the trial got underway, Kelly’s longtime publicist, Regina Daniels, abruptly quit in November 2007, cryptically saying the singer had “crossed a line.” In February 2008, her husband George Daniels told Los Angeles’ KJLH-FM that Kelly had gotten involved with their 21-year-old daughter, Maxine, whom the singer had known since she was 7.

“I confronted him, and he denied it, lied to me to my face,” Daniels said. “Where’s the integrity in a man’s life when he can turn against someone who loved him like I did? It’s a painful thing. It tears at your heart.”

Finally, in May 2008, Kelly’s trial began. After the jury was seated, the prosecution led off by playing the sex tape at the heart of the allegations.

Among the testimonial bombshells: Kelly’s ex-assistant swore it was him in the tape; a dozen prosecution witnesses testified to the girl’s identity; several relatives of the girl alleged to be in it swore for the defense that it wasn’t her; a woman named Lisa Van Allen, who was pregnant on the stand, testified that she engaged in several three-ways with Kelly and the girl on the tape, two of which were recorded; a prosecution expert stated there was no way the tape was a hoax; a defense expert testified that the tape could have been doctored; and Jim DeRogatis, the Sun-Times reporter whom the tape was originally sent to, was scheduled to testify but pleaded the Fifth, meaning he exercised his right to not say anything that might also incriminate him.

After just a few hours of deliberations, on June 13, 2008, Kelly was found not guilty on all charges. Despite the salacious nature of the allegations and the years-long build-up, the trial wasn’t a huge media spectacle when it actually took place, according to numerous reports.

Kelly’s divorce was finalized in 2009. He returned to music, though he had never really stopped, producing a rather prolific amount while under investigation for years, and then he got to work on an autobiography. In his 2012 memoir, Soulcoaster: The Diary of Me, Kelly wrote about being repeatedly sexually abused by a woman, starting when he was 8 years old. When he was about 12, he was approached sexually by a man in the neighborhood, he wrote.

In 2013, Jim DeRogatis, disgusted at music mag Pitchfork for booking Kelly to headline a festival, told The Village Voice in a scathing interview that he had talked to numerous women who had allegedly been preyed on by Kelly over the years, flat-out calling the singer a rapist. “The saddest fact I’ve learned is nobody matters less to our society than young black women,” he said.

Kelly was asked right off the bat about the story in an interview the next day with Atlanta radio station V-103. “I feel like I got the football, man, I’m running towards the touchdown and stopping and looking back, mess around, I’ll get tackled,” he said, per the Huffington Post. “And I also want my fans and everybody out there to know that I really appreciate everybody’s support from the very beginning of my career. But as you know, when you get on top of anything, it’s very windy up there.

“It’s not just about getting on top, it’s about holding your balance once you get up there,” he continued. “You have to be spiritually a climber. So I feel good about [my 12th studio album] Black Panties… As long as I got my fans screaming my name around the world and buying my records, and supporting R. Kelly, everybody who doesn’t agree with it should listen to the last song on Black Panties.”

The song he was referring to is called “Shut Up.”

“I’m going to always have the gift along with the curse,” Kelly told New York magazine in 2015, referring to the onslaught of claims against him over the years. “I feel like I got a million people hating me, I’ve got maybe 8 million loving me. So I’ve got 9 million talking about me, and in a strange, magical way, it keeps me in the game.”

The story was called “The R. Kelly Problem.” But that was hardly groundbreaking. In 2013, The Daily Beast went with, “Why Has the Public Forgiven R. Kelly for His Sordid, Predatory Past?”

Last year, Kelly went public with his new girlfriend, 19-year-old Halle Calhoun, at a party, prompting flashbacks of everything that seems to be wrong with Kelly’s dating history.

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But the Kelly crusade flared again in August when DeRogatis, writing for Buzzfeed News, reported that various concerned parents had alleged that their daughters were living in properties belonging to Kelly and the singer had formed some sort of “cult” and was controlling the girls’ every move.

None of the women are underage and police said there was no investigation because no alleged victims had come forward.

“Mr. Robert Kelly is both alarmed and disturbed at the recent revelations attributed to him,” Kelly’s lawyer told E! News in response to the explosive report. “Mr. Kelly unequivocally denies such allegations and will work diligently and forcibly to pursue his accusers and clear his name.”

Jocelyn Savage, one of the women in question, also spoke up, telling TMZ she was just fine.

“I just mainly want to say that I’m in a happy place with my life,” she said. “I’m not being brainwashed or anything like that. I just want everybody to know—my parents and everybody in the world—that I’m totally fine. I’m happy where I’m at and everything is okay with me.”

DeRogatis wasn’t done, however. In a subsequent report for Buzzfeed News, he detailed the claims of Jerhonda Pace, who was allegedly paid to keep quiet after having sex with Kelly when she was 16. After accepting a settlement she never spoke out via lawsuit as others had before, DeRogatis reported, thereby not adding to the already numerous public allegations against Kelly.

In a statement to E! News Tuesday, a spokesperson for Kelly said, “The allegations against Mr. Kelly are false, and are being made by individuals known to be dishonest. It is clear these continuing stories are the result of the effort of those with personal agendas who are working in concert to interfere with and damage his career. Mr. Kelly again denies any and all wrong doing and is taking appropriate legal action to protect himself from ongoing defamation.”

But is it, after 20 years of disturbing stories about R. Kelly, just too much for this 24/7 Internet age to handle?

After Buzzfeed’s “cult” report, four dates on Kelly’s After Party Tour were canceled due to reported low demand.

Kelly himself mused to New York mag two years ago, referring to the press, “You never know who they gonna get next. I haven’t heard anything negative about me in I don’t know how damn long.”